JPH05112407A - Seed disinfectant - Google Patents

Abstract

PURPOSE:To provide a seed disinfectant having a wide germicidal spectrum and capable of simultaneously controlling seed infectious mycotic diseases and bacterial diseases at low doses. CONSTITUTION:A seed disinfectant contains at least one kind of (E)-4 chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylid ene)-o-toluidine of formula I and penta-4-enyl N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate of formula II and 2-bromo-2-nitropropane-1,3-diol as active ingredients.

Description

Detailed Description of the Invention

[0001]

The present invention relates to (E) -4-chloro-
α, α, α-trifluoro-N- (1-imidazole-
1-yl-2-propoxyethylidene) -o-toluidine and penta-4-enyl N-furfuryl-N
At least one of -imidazol-1-ylcarbonyl-DL-homoalaninate and 2-bromo-2-
The present invention relates to a seed disinfectant containing nitropropane-1,3-diol as an active ingredient.

[0002]

2. Description of the Related Art With the spread of mechanical transplantation of paddy rice, it has become important to grow healthy seedlings during the box raising period. In recent years, in addition to rice scab seedling disease, blast disease, and sesame leaf blight caused by filamentous fungi, the occurrence of bacterial diseases such as rice blight bacterial disease, bacterial wilt disease, and brown stripe disease is a major problem in recent years. Is becoming. Regarding the bacterial disease-causing agent, for example, 2-Bromo-2-nitropropane-1,3-diol is described in Merck Index, 11th Edition, p.
No. 0-105606 discloses a synergistic effect on Lendez trabea when 2-bromo-2-nitropropane-1,3-diol and an ergosterol synthetic inhibitor (EBI agent): prochloraz are combined. Have been described.

By the way, seed disinfection is extremely effective for controlling diseases during seedling raising. Conventionally, in order to control seed infectious diseases, benomyl agents, thiphonate methyl agents, thiuram agents, copper agents, and trifumes are used. Lumisole agents, pefrazoate agents, or mixtures thereof have been used. And regarding the triflumizole agent and the pefrazoate agent, for example, in JP-A-54-119462, (E) -4-chloro-α, α, α-trifluoro-
It has been disclosed that N- (1-imidazol-1-yl-2-propoxyethylidene) -o-toluidine has a seed disinfecting effect against blast disease, sesame leaf blight, linseed scab, etc. In addition, Japanese Patent Laid-Open No. 60-2605
72, penta-4-enyl N-furfuryl-N-imidazol-1-ylcarbonyl-DL-.
It is disclosed that homoalaninate has a seed disinfecting effect against rice blast and sesame leaf blight.

However, the seed disinfectants conventionally used still have problems. For example, regarding benzimidazole drugs that have been widely used in the past, resistant bacteria have appeared in some of the pathogenic bacteria, and it has been reported that the control effect is reduced. In recent years, ergosterol biosynthesis inhibitors such as triflumizole and pefurazoate have begun to be used as effective drugs against benzimidazole-resistant bacteria, but ergosterol biosynthesis inhibitors are highly effective against filamentous fungal disease. Although it showed an effect, it was not expected to be effective against bacterial diseases, so that the antibacterial spectrum was narrower than that of the conventional mixture, and unsatisfactory points were left. Also, as bacterial disease agents, calcium hypochlorite agents, copper agents, etc. have been put to practical use, but the effects are not sufficient, the selectivity is poor, and further mixing with several agents is required. Had a high concentration and had problems such as difficulty in preparing a solution.

[0005]

Therefore, in addition to filamentous fungal diseases, it is effective against bacterial diseases, has a broad antibacterial spectrum, and simultaneously controls these diseases, and is stable against the above resistant bacteria. It was required to develop a low dose of seed disinfectant having the above-mentioned control effect. The present invention has been made in view of such circumstances. Therefore, an object of the present invention is to provide a seed disinfectant having a broad antibacterial spectrum and a stable disease control effect against the above-mentioned resistant bacteria and having a low dose.

[0006]

Means for Solving the Problems As a result of repeated studies by the present inventors, when two specific active ingredients, which have not been known to be used as a seed disinfectant in the past, are used in combination, It was found that the above objects can be achieved and that the disease control effect has a synergistic effect, and the present invention has been completed. Therefore, the seed disinfectant of the present invention is (E) -4-chloro-α, α, α-trifluoro-
N- (1-imidazol-1-yl-2-propoxyethylidene) -o-toluidine (hereinafter, "compound (A)"
And at least one of penta-4-enyl N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate (hereinafter referred to as “compound (B)”) and 2-bromo-2. -Nitropropane-1,3-diol (hereinafter referred to as "compound (C)") is contained as an active ingredient.

The present invention will be described in detail below. Compound (A) which is one of the active ingredients of the seed disinfectant of the present invention
Is represented by the following structural formula (I), and against gray mold, sclerotium disease, seedling blight, powdery mildew, peach scab, corn sesame leaf blight, etc. It is known that it has an effect on the seeds and has a seed disinfecting effect against blast, sesame leaf blight, linseed scab, etc. as described above.

[Chemical 1]

The compound (B) has the following structural formula (I
I), which are rice blast, sesame leaf blight, blight, tomato blight, cucumber powdery mildew, gray mold, powdery mildew of barley, kidney bean kernel disease, of wheat. It is known that it has a controlling effect against leaf rust and a seed disinfecting effect against rice blast and sesame leaf blight.

[Chemical 2]

Furthermore, the compound (C), which is another active ingredient of the seed disinfectant of the present invention, is represented by the following structural formula (III) and is known to be effective as a bacterial agent. There is.

[Chemical 3]

According to the present invention, at least one of the above compounds (A) and (B) and a compound (C)
When and are used as active ingredients, they have a broad antibacterial spectrum and show stable effects against resistant bacteria, and their control effects are remarkably superior to those when used alone, resulting in a synergistic effect. Show the effect. In the seed disinfectant of the present invention, compound (A) or compound (B)
The mixing ratio of at least one of the above and compound (C) is in the range of 1: 0.5 to 1: 100 by weight, and preferably in the range of 1: 0.5 to 1:20.

In order to use the seed disinfectant of the present invention, the above-mentioned active ingredient can be used as it is, but it is usually mixed with a carrier and formulated to be used. In addition, if necessary, various formulation auxiliary agents, for example, surfactants,
A wetting agent, a sticking agent, a thickening agent, a stabilizer and the like may be added to the composition to prepare a dosage form such as a wettable powder, a powder and a flowable agent.

In the seed disinfectant of the present invention, when the above active ingredient is mixed with a carrier, its content is usually in the range of 0.1 to 80% by weight. The carrier of the above formulation, kaolin, attapulgite, bentonite, acid clay, bilophyllite, talc, diatomaceous earth, calcite,
Walnut powder, urea, ammonium sulfate, solid carriers such as fine powder or granules of synthetic hydrous silicon oxide, xylene, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol, cellosolve,
Ketones such as acetone, cyclohexanone, and isophorone,
Examples include vegetable oils such as soybean oil and cottonseed oil, and liquid carriers such as dimethyl sulfoxide, acetonitrile and water.

Surfactants used for emulsification, dispersion, wet extension and the like include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, Naphthalene sulfonic acid formaldehyde condensate, anionic surfactant such as polycarboxylic acid type polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, etc. Examples include nonionic surfactants. As a formulation auxiliary agent, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, C
Examples include MC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), xanthan gum and the like.

When the seed disinfectant of the present invention is used for seed treatment, the formulation is diluted with water to give an active ingredient concentration of 80 to 500.
A 0 ppm solution can be prepared, and seeds can be dipped, sprayed, or seed-dressed in this solution for use. The amount used in the case of seed dressing is usually 0.05 to 5% of the dry seed weight as the amount of the formulation, but the amount used also depends on the form of the formulation and the type of seeds to be treated. Can change. Furthermore, the seed disinfectant of the present invention,
By mixing with other fungicides such as hydroxyisoxazole, a wider range of seed-borne diseases can be controlled. Further, it can be used in combination with thiuram, kasugamycin, thiabendazole, carbendazim, captan, probenazole, benomyl, thiphonate methyl and the like.

Specific examples of diseases for which the seed disinfectant of the present invention is effective include rice blast (Pyricularia).
oryzae), sesame leaf blight (Cochliobolu)
s miyabeanus), fool seedling disease (Gibber)
ella fujikuroi), bacterial blight (Ps)
eudomonas glumae), bacterial seedling blight (Pseudomonas plantarii), brown stripe disease (Pseudomonas avenae), rice scab (Ustilaginoidea viren)
s), wheat leaf blight (Septoria trit)
ici), brown stripe wilt (Leptospheria)
nodorum), lintel smut (Tilletia)
caries), naked smut (Ustilago tr)
itici), seedling wilt (Fusarium s)
p. ), Iris (Cochliobolus sati)
vus), barley leaf spot (Helminthosp)
orium gramineum), naked smut (Ust
ilago nuda), net blotch (Pyrenopho)
ra teres), cloud disease (Rhynchospor)
ium secalis), wilt disease (Septoria)
sp. ), Red smut (Ustilago avena)
e), rye smut (Tilletia carie)
s) and the like.

[0016]

EXAMPLES The present invention will be described in detail below with reference to test examples. Formulation Example 1 (powder) 0.8 parts of compound (A), 2 parts of compound (C), clay 40
Parts and 57.2 parts of talc parts were thoroughly mixed and pulverized to obtain a dust containing 2.8% of the active ingredient.

Formulation Example 2 (powder) 1.6 parts of compound (B), 2 parts of compound (C), clay 40
Parts and 56.4 parts of talc parts were thoroughly mixed and pulverized to obtain a dust preparation containing 3.6% of the active ingredient.

Formulation Example 3 (wettable powder) 2.5 parts of compound (A), 10 parts of compound (C), 5 parts of lignin sulfonate, 3 parts of alkyl sulfonate, and 79.5 parts of diatomaceous earth were well pulverized and mixed. By doing, the active ingredient 1
A wettable powder containing 2.5% was obtained.

Formulation Example 4 (Wettable powder) 5 parts of compound (B), 10 parts of compound (C), 5 parts of lignin sulfonate, 3 parts of alkyl sulfonate, diatomaceous earth 77
By thoroughly pulverizing and mixing the parts, a wettable powder containing 15% of the active ingredient was obtained.

Formulation Example 5 (suspension agent) 8 parts of compound (A), 20 parts of compound (C), 0.5 part of polyoxyethylene nonylphenyl ether, 0.5 part of xanthan gum, polycarboxylic acid type polymer activator (Demol EP (registered trademark)) 1.5 parts, ethylene glycol 8
Part of water and 61.5 parts of water are mixed, and the mixture is wet-milled until the particle size of the mixture becomes 5 μm or less.
A suspension containing 10% was obtained.

Formulation Example 6 (Suspension) 16 parts of compound (B), 20 parts of compound (C), 0.5 part of polyoxyethylene nonylphenyl ether, 0.5 part of xanthan gum, polycarboxylic acid type polymer activator (Demol EP (registered trademark)) 1.5 parts, ethylene glycol 8
Part of water and 53.5 parts of water are mixed, and the mixture is wet-milled until the particle size of the mixture becomes 5 μm or less.
A suspension containing 10% was obtained.

Test Example 1 (Seed Disinfection Effect Test against Rice Blight Bacterial Disease) Rice Blight Bacteria (Pseudomonas gluma)
e) Immersion treatment was performed on the inoculated paddy with a wettable powder prepared according to Formulation Example 3 and Formulation Example 4 for 24 hours, and then 4.5 g per pot was placed in two plastic pots filled with nursery soil. Seeded one by one. Then, the mixture was kept at 30 ° C. for 3 days in a nursery, and then cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (1). Note that a morbidity of 0 means that the patient is not ill, and a morbidity of 1
00 means the same as in the drug-untreated control group.

[Equation 1]

In this test, to help explain the synergistic effect between the active compounds used, the results of the above test were analyzed by RS Colbey, Weeds, Vol. 15, 20-22. Page (1967
Year)). The expected morbidity E (index) was calculated according to the following formula (2). In the formula (2), X and Y represent the morbidity (index) when the two preparations of the active compound are applied separately, and E is the expected morbidity when the mixture of the active compounds is applied. Represent.

[Equation 2] If the actually observed morbidity is smaller than the expected morbidity (E) obtained by the equation (2), it means that there is a synergistic effect.

The results are shown in Table 1.

[Table 1] In Table 1, 1) indicates E obtained by the equation (2).

Test Example 2 (Seed disinfecting effect on paddy infected with rice scab seedling fungus) Rice sprouting seedling fungus (Gibberella fujiku)
roi) was inoculated at the flowering stage of rice, and infected rice was soaked with a wettable powder prepared according to Formulation Example 3 and Formulation Example 24 for 24 hours, and then two seedlings were filled. 4.5 g of each pot was sown in a plastic pot. Then, after keeping at 30 ℃ in the nursery for 3 days,
It was cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (3). Note that a morbidity of 0 means that no disease has occurred, and a morbidity of 100 means that the disease-free control group is the same.

[0026]

[Equation 3] In the following formula (4), X and Y represent the morbidity (index) when two preparations of the active compound are separately applied, and E is the morbidity expected when the mixture of the active compounds is applied. Represents.

[Equation 4]

The results are shown in Table 2.

[Table 2] In addition, in Table 2, 1) indicates E obtained by the equation (4).

Test Example 3 (Simultaneous Control Test of Rice Bacterial Seedling Disease and Rice Bacterial Blight by Seed Disinfection) Rice scabbed seedling fungus (Gibberella fujiku)
roi) against infected paddy obtained by inoculating rice during flowering period,
Pseudomonas gluma
e) was inoculated to prepare diseased paddy infected with both diseases.
The suspension prepared according to Formulation Example 5 and Formulation Example 6 was 2
Immersion treatment was performed for 4 hours, and then, 4.5 g per pot was sown in two plastic pots filled with seedling raising soil. Then, the mixture was kept at 30 ° C. for 3 days in a nursery, and then cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (5). Note that a morbidity of 0 means that no disease has occurred, and a morbidity of 100 means that the disease-free control group is the same.

[0029]

[Equation 5]

The results are shown in Table 3.

[Table 3]

[0031]

EFFECTS OF THE INVENTION The seed disinfectant of the present invention exerts a high effect against various seed-borne diseases, and exceeds the effects when each component is used alone, and can reduce the amount of active ingredient. Is. In addition, the antibacterial spectrum is wide,
It is possible to control filamentous fungal diseases and bacterial diseases at the same time, reduce the work for disinfecting seeds, and at the same time, suppress the occurrence of diseases that cause problems during the seedling raising period.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display area A01N 33:20)

Claims (1)

[Claims] 1. (E) -4-Chloro-α, α, α-trifluoro-N- (1-imidazol-1-yl-2-propoxyethylidene) -o-toluidine and penta-4-enyl. N-furfuryl-N-imidazole-
At least one of 1-ylcarbonyl-DL-homoalaninate and 2-bromo-2-nitropropane-
A seed disinfectant comprising 1,3-diol as an active ingredient.